Isopropylamine → 5-{3-(Cyanomethyl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-N-isopropylpyridine-2-carboxamide

HRID 571480Notes

Reaction equation

HRID 571480 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.[CH3:11][CH:12]([NH2:14])[CH3:13].Cl.Cl.C[Si](C)(C)CCOC[N:23]1[C:27]2[N:28]=[CH:29][N:30]=[C:31]([C:32]3[CH:33]=[N:34][N:35]([C:37]4([CH2:41][C:42]#[N:43])[CH2:40][NH:39][CH2:38]4)[CH:36]=3)[C:26]=2[CH:25]=[CH:24]1>>[C:42]([CH2:41][C:37]1([N:35]2[CH:36]=[C:32]([C:31]3[C:26]4[CH:25]=[CH:24][NH:23][C:27]=4[N:28]=[CH:29][N:30]=3)[CH:33]=[N:34]2)[CH2:40][N:39]([C:2]2[CH:3]=[CH:4][C:5]([C:8]([NH:14][CH:12]([CH3:13])[CH3:11])=[O:10])=[N:6][CH:7]=2)[CH2:38]1)#[N:43]

Participants

4

Reactant 3

HCID 6363IsopropylamineHCID 6085445-Bromopyridine-2-carboxylic acidHCID 67391464{3-[4-(7-{[2-(Trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile dihydrochloride

Product 1

HCID 711435705-{3-(Cyanomethyl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-N-isopropylpyridine-2-carboxamide

Procedure

This compound was prepared by using procedures analogous to those described for the synthesis of Example 3, Step 1-3 starting from 5-bromopyridine-2-carboxylic acid, 2-propanamine and {3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile dihydrochloride. LCMS (M+H)+: m/z=442.2. 1H NMR (400 MHz, DMSO-d6): δ 12.82 (s, 1H), 9.12 (s, 1H), 8.88 (s, 1H), 8.59 (s, 1H), 8.12 (d, J=8.0 Hz, 1H), 7.94 (d, J=2.5 Hz, 1H), 7.86 (d, J=8.0 Hz, 1H), 7.83 (m, 1H), 7.28 (m, 1H), 7.10 (dd, J=8.0, 3.0 Hz, 1H), 4.66 (d, J=8.0 Hz, 2H), 4.41 (d, J=8.0 Hz, 2H), 3.78 (s, 2H), 4.05 (m, 1H), 1.16 (d, J=6.5 Hz, 6H).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-994ab443b56f4445abf50b75269c09e8
Source dataset
uspto-grants-2015_05
Patent number
US09023840B2

Reaction notes

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